US5270371A - Adhesive compositions for electronic packages - Google Patents
Adhesive compositions for electronic packages Download PDFInfo
- Publication number
- US5270371A US5270371A US07/955,776 US95577692A US5270371A US 5270371 A US5270371 A US 5270371A US 95577692 A US95577692 A US 95577692A US 5270371 A US5270371 A US 5270371A
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- US
- United States
- Prior art keywords
- substrate
- composition according
- silica
- solvent
- conductive metal
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/48—Arrangements for conducting electric current to or from the solid state body in operation, e.g. leads, terminal arrangements ; Selection of materials therefor
- H01L23/488—Arrangements for conducting electric current to or from the solid state body in operation, e.g. leads, terminal arrangements ; Selection of materials therefor consisting of soldered or bonded constructions
- H01L23/498—Leads, i.e. metallisations or lead-frames on insulating substrates, e.g. chip carriers
- H01L23/49866—Leads, i.e. metallisations or lead-frames on insulating substrates, e.g. chip carriers characterised by the materials
- H01L23/49883—Leads, i.e. metallisations or lead-frames on insulating substrates, e.g. chip carriers characterised by the materials the conductive materials containing organic materials or pastes, e.g. for thick films
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1057—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain
- C08G73/1064—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain containing sulfur
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/0001—Technical content checked by a classifier
- H01L2924/0002—Not covered by any one of groups H01L24/00, H01L24/00 and H01L2224/00
Definitions
- This invention relates to adhesive compositions, and more particularly to compositions useful in multichip electronic packages.
- a "chips first" high density interconnect system is described in U.S. Pat. Nos. 4,783,695 and 4,918,811; in its construction, the chips are placed on a substrate and the interconnect structure is then laid down as an overlay.
- chips last is also a “chips last” system, in which the chips form an overlay on thin film dielectric and patterned metal regions.
- chip cavities are cut in a ceramic substrate and power and ground lines and I/O pads are formed on the surface of the ceramic by depositing, patterning and etching conductive metal layers. Silicon chips are then bonded in the cavities with a thermoplastic adhesive, a process generally known as "die-attach”.
- a polyimide sheet is laminated over the chip-filled substrate and vias are drilled through the polyimide to the chip pads, which are located by laser action.
- Conductive films are then deposited, patterned and etched to produce interconnects. This last process is typically repeated to produce a multilayer overlay.
- Die-attach adhesives used in high density interconnect systems include both conductive and non-conductive materials, with conductive adhesives being used when grounding of the chip is desired. Both thermoplastic and thermosetting resins may be employed in such adhesives. The use of a thermoplastic resin is often preferred because it permits defective chips to be removed and replaced. When a thermosetting adhesive is used, there is no way to remove a damaged chip without severely damaging the substrate. With thermoplastic adhesives, it is possible to peel off the overlay carefully, heat the substrate to melt the adhesive, remove the chip and replace it with an undamaged one. Such a repair scheme is disclosed, for example, in U.S. Pat. No. 4,878,991.
- polyimides are in use as thermoplastic die-attach adhesives.
- polyetherimides prepared from 2,2-bis[4-(3,4-dicarboxyphenoxy)phenyl]propane dianhydride, also known as “bisphenol A dianhydride", and bis(4-aminophenyl) sulfone.
- BPADA-SDAN polyetherimides such polyimides will be referred to hereinafter as "BPADA-SDAN polyetherimides”. They may be employed as such or as the polyamic acid precursors.
- BPADA-SDAN polyetherimides One advantage of the use of BPADA-SDAN polyetherimides is their very high glass transition temperature, on the order of 250° C., and their high melt viscosity. This permits the chip to be accurately and immovably placed, facilitating laser location of the pad with certainty.
- Typical die-attach adhesive compositions have been formulated by dissolving the BPADA-SDAN polyetherimide in such solvents as acetophenone, to form a viscous solution which may be applied to the substrate in a dot pattern, with a unique system of dots provided for each chip. Following die-attach, the package is heated to evaporate the solvent, leaving the polyetherimide to serve as the actual adhesive material.
- the adhesive increases in viscosity too rapidly for convenience.
- acetophenone solutions of BPADA-SDAN polyetherimides may begin to dry after as little as 6 minutes, which is too short a time for die-attach to be completed.
- loss of adhesion of the chips to the ceramic substrate may occur and may not be noticed until a later processing stage, requiring inconvenient and expensive reworking.
- the present invention provides adhesive compositions with sufficient melt viscosity to function as chip adhesives, as well as working times sufficiently long to ensure reliable die-attach.
- the adhesive is thermoplastic, facilitating replacement of defective chips.
- the adhesive compositions have thixotropic properties, minimizing chip motion and the required thickness of the adhesive layer.
- thermoplastic adhesive compositions consisting essentially of:
- polyetherimide consisting essentially of structural units of the formula ##STR1## at least one of silica and conductive metal particles in an amount to provide thixotropic properties and conductivity, respectively, or polyamic acid precursor thereof;
- the polyetherimide employed in the adhesive compositions of this invention is the aforementioned BPADA-SDAN polyetherimide, which, as previously described, may be employed in the form of the final polyimide or its polyamic acid precursor. Upon heating, the polyamic acid loses water with conversion to the polyimide.
- silica is present in the adhesive composition.
- Silica is present as a thixotropic agent, minimizing chip motion and the required glue line thickness of the adhesive layer between the chip and the substrate.
- silica should be employed in extremely small particle size, exemplified by fumed silica and colloidal silica. Fumed silica is preferred, with hydrophobic fumed silica being especially preferred by reason of its low tendency to absorb ambient moisture. Hydrophobic silica may be prepared by treating ordinary silica with a polydimethylsiloxane fluid or the like.
- a conductive die-attach adhesive is desired, the presence of conductive metal particles is necessary. Any suitable conductive metal may be employed; silver and gold are examples, with silver often being preferred. It is normally employed in flake form, the flakes typically having dimensions on the order of 0.5-10 microns.
- the solvent employed according to the present invention is a crucial feature thereof. It is at least one mono- or disubstituted acetophenone, the substituents being methyl, ethyl, methoxy or ethoxy groups.
- Suitable acetophenones include 4-methylacetophenone, 3-methylacetophenone, 3,4-dimethylacetophenone and 3-methoxyacetophenone, which have boiling points between 210° and 250° C.
- 4-Methylacetophenone (b.p. 226° C.) is generally preferred by reason of its relatively low cost and particular effectiveness.
- the proportion of silica in the adhesive compositions of this invention is an effective amount to provide thixotropic properties. It is typically about 1-25% by weight, based on total solids; i.e., on total composition excluding solvent.
- the conductive metal is present in an amount effective to provide conductivity, typically about 55-75% by weight based on total solids.
- the solvent is present in an amount effective to provide the desired melt viscosity and workability. It usually comprises about 55-85% of total composition including solvent.
- compositions of this invention may also contain other materials which do not materially affect their basic and novel characteristics.
- Such materials may include, for example, substances added to improve thermal conductivity.
- Illustrative substances of this type are aluminum nitride powder and diamond powder.
- Another aspect of the invention is an electronic circuit structure comprising a substrate, usually a ceramic such as alumina, aluminum nitride or aluminum-silicon carbide composite or a metal or metalloid such as iron-nickel-cobalt-manganese alloy or silicon, and at least one integrated circuit chip adhered to said substrate with an adhesive composition as described hereinabove.
- a plurality of chips is usually present, with an interconnect pattern, preferably comprising thin film dielectrics and patterned metal interconnections as previously described, provided therefor.
- the adhesive compositions thus prepared were dispensed in conventional manner on an alumina substrate and chips placed thereon after various time increments. It was found that the working times of the adhesive compositions were on the order of 19 minutes. Control samples, in which the 4-methylacetophenone was replaced by acetophenone, had working times only on the order of 6 minutes.
Abstract
Description
______________________________________ Example 1 2 3 ______________________________________ BPADA-SDAN polyetherimide, %.sup.1 80 33 32.6 Silica, %.sup.1 20 2.2 Silver flakes, %.sup.1 67 65.2 4-Methylacetophenone, %.sup.2 82 65.4 65 ______________________________________ .sup.1 Excluding solvent. .sup.2 Including solvent.
Claims (14)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/955,776 US5270371A (en) | 1992-10-02 | 1992-10-02 | Adhesive compositions for electronic packages |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/955,776 US5270371A (en) | 1992-10-02 | 1992-10-02 | Adhesive compositions for electronic packages |
Publications (1)
Publication Number | Publication Date |
---|---|
US5270371A true US5270371A (en) | 1993-12-14 |
Family
ID=25497311
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US07/955,776 Expired - Lifetime US5270371A (en) | 1992-10-02 | 1992-10-02 | Adhesive compositions for electronic packages |
Country Status (1)
Country | Link |
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US (1) | US5270371A (en) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5552633A (en) * | 1995-06-06 | 1996-09-03 | Martin Marietta Corporation | Three-dimensional multimodule HDI arrays with heat spreading |
EP0777274A1 (en) | 1995-11-30 | 1997-06-04 | Lockheed Martin Corporation | A high density interconnected circuit module with a compliant layer as part of a stress-reducing molded substrate |
EP0805616A1 (en) * | 1996-05-03 | 1997-11-05 | International Business Machines Corporation | Electrically conductive compositions |
US5866044A (en) * | 1994-11-15 | 1999-02-02 | International Business Machines | Lead free conductive composites for electrical interconnections |
US5880181A (en) * | 1993-12-27 | 1999-03-09 | Akzo Nobel Nv | Gels of organic peroxides |
US20080248258A1 (en) * | 2007-04-06 | 2008-10-09 | Fukui Precision Component (Shenzhen) Co., Ltd. | Mounting support for retaining a flexible printed circuit board |
US7473618B1 (en) | 2008-04-22 | 2009-01-06 | International Business Machines Corporation | Temporary structure to reduce stress and warpage in a flip chip organic package |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3501443A (en) * | 1968-05-20 | 1970-03-17 | American Cyanamid Co | Process for preparing a polyimide comprising reacting 3,4 - dicarboxy - 1,2,3,4-tetrahydro - 1 - naphthalene succinic dianhydride with a diprimary diamine in the presence of certain organic solvents |
US3607814A (en) * | 1969-02-17 | 1971-09-21 | American Cyanamid Co | Composition of matter comprising a solution of a polyimide in a mixture of solvents |
US4377652A (en) * | 1978-02-17 | 1983-03-22 | Asahi Kasei Kogyo Kabushiki Kaisha | Polyamide-imide compositions and articles for electrical use prepared therefrom |
US4495321A (en) * | 1983-12-19 | 1985-01-22 | Atlantic Richfield Company | Polyimide and/or polyamide-imide compositions in mixed solvents |
US4565858A (en) * | 1984-10-26 | 1986-01-21 | General Electric Company | Polyetherimides with high thermal stability and solvent resistance and precursors therefor |
US5019535A (en) * | 1989-03-28 | 1991-05-28 | General Electric Company | Die attachment method using nonconductive adhesive for use in high density interconnected assemblies |
US5145899A (en) * | 1991-02-28 | 1992-09-08 | E. I. Du Pont De Nemours And Company | Polymers modified by ketonic and ether-ketonic compounds |
-
1992
- 1992-10-02 US US07/955,776 patent/US5270371A/en not_active Expired - Lifetime
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3501443A (en) * | 1968-05-20 | 1970-03-17 | American Cyanamid Co | Process for preparing a polyimide comprising reacting 3,4 - dicarboxy - 1,2,3,4-tetrahydro - 1 - naphthalene succinic dianhydride with a diprimary diamine in the presence of certain organic solvents |
US3607814A (en) * | 1969-02-17 | 1971-09-21 | American Cyanamid Co | Composition of matter comprising a solution of a polyimide in a mixture of solvents |
US4377652A (en) * | 1978-02-17 | 1983-03-22 | Asahi Kasei Kogyo Kabushiki Kaisha | Polyamide-imide compositions and articles for electrical use prepared therefrom |
US4495321A (en) * | 1983-12-19 | 1985-01-22 | Atlantic Richfield Company | Polyimide and/or polyamide-imide compositions in mixed solvents |
US4565858A (en) * | 1984-10-26 | 1986-01-21 | General Electric Company | Polyetherimides with high thermal stability and solvent resistance and precursors therefor |
US5019535A (en) * | 1989-03-28 | 1991-05-28 | General Electric Company | Die attachment method using nonconductive adhesive for use in high density interconnected assemblies |
US5145899A (en) * | 1991-02-28 | 1992-09-08 | E. I. Du Pont De Nemours And Company | Polymers modified by ketonic and ether-ketonic compounds |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5880181A (en) * | 1993-12-27 | 1999-03-09 | Akzo Nobel Nv | Gels of organic peroxides |
US5866044A (en) * | 1994-11-15 | 1999-02-02 | International Business Machines | Lead free conductive composites for electrical interconnections |
US6197222B1 (en) | 1994-11-15 | 2001-03-06 | International Business Machines Corporation | Lead free conductive composites for electrical interconnections |
US5552633A (en) * | 1995-06-06 | 1996-09-03 | Martin Marietta Corporation | Three-dimensional multimodule HDI arrays with heat spreading |
EP0777274A1 (en) | 1995-11-30 | 1997-06-04 | Lockheed Martin Corporation | A high density interconnected circuit module with a compliant layer as part of a stress-reducing molded substrate |
US5866952A (en) * | 1995-11-30 | 1999-02-02 | Lockheed Martin Corporation | High density interconnected circuit module with a compliant layer as part of a stress-reducing molded substrate |
EP0805616A1 (en) * | 1996-05-03 | 1997-11-05 | International Business Machines Corporation | Electrically conductive compositions |
US20080248258A1 (en) * | 2007-04-06 | 2008-10-09 | Fukui Precision Component (Shenzhen) Co., Ltd. | Mounting support for retaining a flexible printed circuit board |
US7473618B1 (en) | 2008-04-22 | 2009-01-06 | International Business Machines Corporation | Temporary structure to reduce stress and warpage in a flip chip organic package |
US7538432B1 (en) | 2008-04-22 | 2009-05-26 | International Business Machines Corporation | Temporary structure to reduce stress and warpage in a flip chip organic package |
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Legal Events
Date | Code | Title | Description |
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AS | Assignment |
Owner name: GENERAL ELECTRIC COMPANY, NEW YORK Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNORS:COLE, HERBERT S.;WILSON, JAMES W.;REEL/FRAME:006281/0361;SIGNING DATES FROM 19920928 TO 19920929 |
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Owner name: MARTIN MARIETTA CORPORATION, MARYLAND Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:GENERAL ELECTRIC COMPANY;REEL/FRAME:007046/0736 Effective date: 19940322 |
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Owner name: LOCKHEED MARTIN CORPORATION, MARYLAND Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:MARTIN MARIETTA CORPORATION;REEL/FRAME:008628/0518 Effective date: 19960128 |
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